This week we read Parshat Zachor, as we do every year on the Shabbat preceding Purim. The special reading is taken from the end of Parshat Ki Tetzei, directly following the exhortation to be honest in one’s business dealings and not to have two sets of weights or measures. Rashi sees a logical progression between the themes. In the second pasuk of Parshat Zachor, we learn that the enemy, Amalek, attacked “those who were trailing behind” (Devarim 25:18). Rashi explains that these individuals were weakened as a consequence of their wrongdoing. Indeed, the Maharal in Gur Arye says in the name of Sifri that these individuals turned away from Hashem and lost the protection of His “enveloping wings.”
Rashi also suggests that from the word “karcha,” we learn three ways in which Israel was found morally wanting and subject to the predation of Amalek: 1) according to its most literal meaning, namely, that things just happen, the people did not accept Divine Providence but instead believed in coincidence, thus allowing themselves to become subject to the laws of nature; 2) from the root kuf-reish (kor), meaning cold, Israel’s passion for serving Hashem “cooled off”; and 3) from the word keri – that they behaved with sexual licentiousness or, as the Maharal explains in Gur Arye, inverted the proper roles of men and women in society and spirituality.
The laws of weights and measures are the specific context in which we learn of the assault of Amalek in the retelling read as Parshat Zachor. When the episode is introduced (ibid. 25:17), Rashi explains that if somebody is dishonest with their weights and measures, they should worry about the depredations of their enemies, for they have made themselves vulnerable, bringing calamity upon themselves. Specifically referencing the Midrash Tanchuma, he cites a verse in Mishlei )11:2): “Come with wickedness, then catastrophe will come.”
The Maharal explains in Gur Arye that dishonesty and falsehood are a crime against the order of the universe. Hashem created a world where everything has its proper place and measure; everything has been determined in advance and provided for all Creation. Therefore, when a person plays fast and loose with measurements and boundaries, he creates a space for the enemy to pounce. The enemy here refers both to a physical enemy as well as the spiritual Enemy who endeavors to upset the spiritual balance of men and women in order to destroy them and take their souls (Bava Batra 16a).
Individual humans upset the balance on their own, Rashi is saying, and thereby provide an opening for the enemy. The Maharal elaborates on this, citing another source in Bava Batra (88b) that indeed the punishment for cheating in business is more horrible than that for sexual immorality. In fact, he explains, if somebody cheats many people, it might not be possible for him to do teshuva at all because he will not know to whom he must return all the money he stole. In conclusion, he brings the Midrash Tanchuma that Rashi had alluded to regarding a dishonest individual, and warns that an entire generation engaging in rapacious and unethical business dealings will come to suffer the yoke of foreign tyrants.
The Maharal explains that if a society has become so perverted that people are no longer ashamed to falsify business transactions and counterfeit measures, the only suitable outcome to restore the balance is for them to get exactly what they deserve – to be, as it were, put in their place by the enemy, who is actually the servant of Hashem, in order to return order to His universe.